Anthraquinone vat dyestuffs



UNITED STATES NrnnAoUr onE VAT DYESTUFFS Raymond Joseph Sobatzki, SouthMilwaukee,

. r. :Wis and Oakley Maurice Bishjo'p, deceased] I lateoi Wilmington,DeL, by Eva :1. Bishop and Wilmington Trust 00., executors, Wilmington,

Del". assignor's to E. I. du'Pont de Nemours "& Company, Wilmington,Del., a corporation of, 1..

- Delaware No Drawing. Application May "9,, 724,820

4 Claims. (01. 260-44),

This invention relates to the preparation of new and valuable dyestufisof the anthraquinone series and more particularly to the preparation ofp-acidylaminobeta phenyl-anthraquinoneof the general formula:

wherein the R represents an aromatic radical and in which theanthraquinone radical may contain simple monovalent substituents.

The inventors have found that p-amino-betaphenyl-anthraquinone can becondensed with. acid chlorides of, the. aromatic series to form newproducts which dye fibers in bright shades rangingfrom greenish-yellowto orange of good fastness to light, Washing and bleach.

The procedure used for effecting these condensations is in general thesame as usually used in the preparation of aroyl-amino-anthraquinonecompounds by condensing amines with acid chlorides, which may beillustrated by thefollowing examples.

Example 1 10 parts of p'-amino-beta phenyl-anthraquinone are suspendedtogether with 10 parts of 1,9-anthraisothiazol-2-carbonyl chloride ,in300 parts of nitrobenzene. The mixture is heated to -145 for 30minutes,then cooled to 40 and filtered,washed and dried. The resultingcondensation product is a greenish-yellow powderand dyes cotton from aviolet-blue to blue vat in greenish-yellow shades of good fastness. Theproduct has the following probable formula:

934;, serial Emm jz 10 parts.- of 'p -amino beta phenyl-anthra=quinoneare sus'pendedin 250; parts of ,nitrobenzene and 11.5partsofl,9-anthraisoselena.zol-2- carbonyl chloride, are added.:.1Thetemperature is raised to ,l'40? and maintained for 1- hour. Aftercooling, the dyestufiis isolated by filtration andpwashe'dn It. is aE-yel-lowpowder 'd'yeingcotton in yellow shades. q I I I f mmv fr'. I

10 parts of p-amino-beta-phenyl-anthraquinone are dissolved in 150 partsof trichlorbenzene at 130 and a solution of 10 parts of 1,9-thiophenoanthrone-Z-carbonyl chloride in 150 parts of trichlorbenzene;is added. The temperature is raised to -150 and maintained for /z hour.After cooling, the dyestuff is filtered and washed. It dyes cotton froma reddishbrown vat in golden yellow shades, and has the probableformula:

Example 4 I reduced with '75 parts of sodium sulfide at the boil. Duringthe course of the reduction the alcoholis evaporated (2-3 hours) and thered amino compound filtered hot, washed and dried.

It may be benzolated as follows: 20 parts of amino compound are heatedwith 250 parts of nitrobenzene and 15 parts of benzoyl chloride to -160for 1 hour. The yellow crystalline product is filtered at 50, washedwith alcohol and dried. It dissolves in concentrated sulfuric acid withyellow color and dyes cotton in yellow the following probable formula:

shades from ared brown vat. The product has acid chloride, pyridine acidchloride, picolinic acid chloride, quinoline acid chloride, etc. By

7 Example i I v parts of p-aminoEbeta-phenyl-anthra quinone and 150parts of nitro'benzene are heated I to ISO-160 and 5.2 parts of benzoylchloride are added over a period of -30. minutes; The reactionmixturegis cooledto 30-'40 and filtered.

The product, on drying, is a bright yellow powder dyeing cotton a yellowshade from a brown vat;-

Any of the methods known iri the a'rtfor' condensing arylamino compoundswith aroyl ch1 o- I rides may be used in place of those specificallydescribed in the examples; which are given merely to illustratea nd'nottolimit the invention. Vari0us" solyentsrnay be usedinplac ofnitrobenzene or itrichloroberizene and the temperaturesfimaybeiivariedwidely.

' Other acid 'chloridesthan those-mentioned in the eka'mples maybeemployed in the production of dyestuffs of thisseries, such asbeta-naphthoyl chloride, the Bz-substitution products of benzoylchloride, anthraquinone a cid chlorides substi-' tuted or unsubstitutedacidchlorides of heterocyclic aromatic 'compounds"such asfthiophenetheterrn aroyl as it is used in the claims it is 0 v. SN H H 0 ll 4. Theprocess which comprises condensing a 4'amino-2phenyl-anthraquinone withan aroyl halide.

RAYMOND J. SOBATZKI. EVA P. BISHOP, WILMINGTON TRUST CO., By W. J.LAIRD, V. P; Emecutors of the Estate of Oakley Maurice Bishop,

Deceased. v

